The Adventures of Nate and Jenny
by LadyChaceBass
Summary: Nate and Jenny rekindle their friendship, and hopefully it blossoms into something more. -Chuck and Jenny friendship included.-
1. Chapter 1

Authors note. This was just a little mess around, I was pretty high when I wrote this. So it's not to be taken too seriously, just thought it would be a laugh. This is loosely based in season 2, some events don't exactly match up, Jenny still doesn't know about the letter and Nate still thinks she ignored it. Jake is O/C. No beta, all mistakes are mine. Au bitchesssssss.

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><p>Adventure one.<p>

"Damn it." Jenny huffed as she shoved her cell phone back into her pocket and rested her head against wall outside of her school.

"Good morning, Jennifer." Chuck smirked and nodded. "Lover boy not answering the phone?" He said as he gestured to her pocket.

"Hey Chuck." Jenny smiled greeting her close friend. Although she wasn't quite sure how they became so close, they both confided in each other a lot and occasionally hung out. "It's not Jake, it's my guy." Jenny widened her eyes and added more emphasis on the word 'guy', talking about her dealer.

"Ah." Chuck nodded, he and Jenny often got high together when neither of them had anything better to do. "Running out of weed are we?"

"Yeah. Know where I can get some?" She asked, of course he knew someone.

"Have you tried Nathaniel?" Chuck asked.

"Nate?" Jenny laughed.

"Yes. What's funny?" Chuck cocked a brow.

"Since when did he start selling weed? Jenny asked, turning more serious.

"Only recently, seeing as he's still trying to repair the damages his father left him with." Chuck joined her leaning against the wall.

"Oh, right." Jenny nodded understandingly. She and Nate hadn't spoken much since he came back from the Hampton's, he just left without even trying to contact her, which bummed her out. When he came back he got back with Vanessa, not giving Jenny a chance to speak with him. That had been a few months back now and she was back in school. They smiled and made small talk when they were together because they all shared the same group of friends, but they never spoke about what happened between them. Jenny was still completely oblivious to the fact he had written her a letter.

"Would you like to get some for you, or can you manage it yourself?" Chuck asked, understanding that she and Nate weren't exactly the closest of friends.

"Nah it's cool, I'll catch up with him at lunch or something." Jenny said, she couldn't avoid him forever. She was totally over him now anyway, she had Jake and he had Vanessa. They were good friends before they kissed, what was stopping them from being friends again?

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><p>"Nate!" Jenny called as she ran towards him.<p>

"Oh, hey Jenny." Nate smiled awkwardly.

"Hey. Can I talk to you?" She gave a shy smile.

"Sure. What's up?" Nate continued walking with Jenny beside him.

"So I hear that your, you know..." She lowered her voice to a husky whisper. "...dealing?" They both cautiously looked around them.

"Yeah." Nate pursed his lips together and nodded.

"Got anything I can buy?" Jenny smirked.

"I didn't know you smoked?" Nate chuckled.

"You don't brag about selling, I don't brag about smoking." Jenny laughed.

"True." Nate laughed. They came to a stop at the top of the steps where Blair and her groupies usually sat. "So what you after?"

"What you got?" She asked.

"White Widow, Bubblegum Kush, Silver Haze...oh!" Nate exclaimed lowering his voice. "I just got some 'Special Queen' imported in. It's awesome, I recommend it." Nate smirked.

"Special Queen it is then." Jenny laughed.

"Great choice. I don't bring that stuff to school with me, that's mainly for me but it's totally cool if you want some. I can bring it to you or you can come get it from me after school?" Nate said.

"I can stop by your place, my dad's gonna be home so it'll be awkward if you show up like 'oh hey Rufus, I'm just here to sell Jenny some weed'." Jenny laughed uncontrollably.

"Hey, maybe he wants some. Those band guys are pretty hardcore." Nate smirked suggestively and shrugged his shoulders before laughing along with Jenny.

"So, yours it is then?" She asked, after catching her breath.

"Okay sure. You still have my number?" Nate asked, Jenny bit her lip awkwardly.

"No, uh...new phone, same number though." She said awkwardly, not wanting him to know she deleted his number as soon as she found out he was back with Vanessa.

"I still have yours..." Nate pulled out his phone and after a minute Jenny's phone rang.

"And now I have yours." Jenny smiled.

"What time should I come?" Jenny asked.

"Three thirty good?" Nate asked.

"We finish school at 3, by the time I get to Brooklyn and then go to yours It'll be like, four." Jenny laughed.

"Why don't you just come with me after school?" Nate asked.

"Makes sense." Jenny agreed, before Vanessa approached, pulling Nate in for a long, rough kiss.

"Oh Jenny. Didn't notice you there." Vanessa said condescendingly.

"I'm sure you didn't." Jenny pursed her lips and nodded sarcastically.

"What were you talking about?" Vanessa asked nosily.

"Maths." Jenny said.

"Exams." Nate said at exactly the same time as Jenny.

"Maths...exams." Jenny amended, looking wide eyed at Nate.

"Uh...yeah. The ones we have coming up." Nate lied, keeping a cool exterior. Jenny just smirked at Nate and he smiled shyly causing Vanessa to glare at Jenny. If looks could kill, Jenny thought. She'd noticed that Vanessa showed up at school every lunch time to check in on Nate lately, she and Vanessa were still on bad terms.

"Later, Nate." Jenny smiled, causing Vanessa to scoff.

"Bye." He smiled back.

"Oh actually Jenny, Dan's invited me over for dinner tonight. Nate and I had plans so I guess he's coming too." Vanessa said, wrapping a possessive arm around Nate's waist smirking, causing him to shift uncomfortably.

"I have plans with Jake, so I won't be there. But enjoy." Jenny lied, not wanting Vanessa to know she was actually meeting Nate. Jenny was no longer phased by Vanessa's stupid attempts at making her jealous, she was over it but she just hated Vanessa for going behind her back and constantly rubbing it in.

"About that, I can't make it. I have other plans..." Nate tried to quickly think of an excuse, "My mom." Nate nodded. "I'm visiting my Dad in jail with my mom."

"Can I come?" Vanessa asked attempting to seem sweet, but only making herself look clingy, Jenny bit her lip to hold back the laughter.

"No, family stuff. Sorry." Nate offered a polite yet nervous smile.

"It's cool, I understand babe." Nate couldn't help but cringe a little, did she really just call him babe?

"Later, babe." Jenny laughed before walking away.

"God she's so annoying." Vanessa said in utter disgust.

"Come on, she's my friend." Nate said, trying to defend Jenny. He took a second to think about their conversation and how they seemed as though they were on the road to friendship.

"You don't need to be friends with her, you have me." Vanessa said stubbornly. Why was she suddenly being so possessive and clingy?

"Whatever, I have to get back to class." And with that Nate shook his head and turned quickly on his heels. Since they'd gotten back together, things hadn't been the same. She wasn't as cool as she acted, he'd been noticing some big changes in her, and not for the better.

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><p>Nate pulled out his phone and propped his book on 'Of Mice and Men' up in front of him and pretended to read as he began texting.<p>

_**N: Meet me at the gates after class and we'll go :) **_

He flicked through his contacts and sent it to Jenny, wondering if the smiley face was too much.

_**J: Cool. :)**_

She put one back, guess it wasn't that bad then. He was kind of happy that they were building their friendship up again, even after she totally ignored his letter, he guessed it would be better if he didn't mention it. It took them three whole months to even say hello to each other, now five months after the incident, he'd rather not dig up the past and ruin their friendship again.

Jenny sniggered at the smiley face at the end of his text, but she put one back anyway. She was happy that they were re-building their friendship, even though he totally blew her off, she thought it would be best to get over it and leave it in the past, where it belongs.

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><p>"Hey." Nate smiled as he approached Jenny, who stood waiting for him.<p>

"Hey." She smiled back.

"I am so ready to get stoned right now." Nate chuckled as he rubbed his hands together.

"So am I." Jenny shook her head and laughed. "This places bores me to death, I'm surprised I lasted a whole day with only one joint."

"I know the feeling." Nate laughed.

"Won't your mom like, kill you if she found out you were selling weed?" Jenny asked, curiously.

"She always stays in the Hampton's so she's never home. It's usually just me, plus I'm not like a hardcore dealer. I only sell to friends, mainly Chuck, and a few other people. Nothing serious, just some extra cash." Nate informed her as they got into a taxi and made their way to his house. While in the Taxi they made small talk about their friends and school.

"Thanks man." Nate smiled handing the taxi driver some cash before he and Jenny got out of the taxi.

"I could give you some money..." Jenny said before being cut off by Nate's laughter.

"Jenny I have money again, you know? Our bank accounts are no longer frozen over." Nate laughed.

"I was only being polite." Jenny raised her hands in mock surrender laughing. They went to his house and straight to his room.

"How much do you want?" Nate asked.

"An ounce." Jenny said, Nate weighed out the weed and put it into a druggie bag, the extra amount he added didn't go un-noticed. Jenny handed him the cash.

"Thanks." She smiled, throwing her back pack over her shoulder and she turned away to leave.

"You're not gonna stay and smoke with me? C'mon." Nate laughed. Not quite ready to say goodbye just yet. He forgot how nice it was to hang out with her.

"Okay, fine." Jenny laughed, she was hoping he'd ask her to stay, she was enjoying hanging out with him. She began rolling a joint as did Nate.

"Rolled up?" Nate asked.

"Yeah, we going outside to smoke?" Jenny asked.

"Nah, we'll stay here. Could you crack open the window?" Nate asked as he finished rolling his own spliff. Jenny did before taking a seat and Nate pulled out an ashtray. They both smirked before lighting up their joints.

"Oh shit." Jenny coughed exhaling the smoke,

"I coughed the first time too. Good, right?" Nate smirked.

"Yeah." Jenny nodded.

"So, tell me about your boyfriend, what his name again?" Nate said.

"Jake." Jenny smiled. "He has ash-blonde hair, and awesome jaw line, he's British and he has blue eyes."

"That's a description of him." Nate laughed. "I mean, what's he like."

"Oh." Jenny laughed. "He's a really cool guy, he plays guitar. He's your age, 17. He goes to Dalton academy, he's smart, he's funny..." Jenny trailed off thinking about Jake in a stoned haze, he really was perfect. He even taught her how to play guitar.

"He seems pretty cool." Nate smiled, happy for Jenny but felt a strange pang in his stomach when he saw the content smile on her face as she spoke fondly of Jake.

"But he's not around much. I mean, when he is he makes up for it but his hearts set on Yale so he's always studying and stuff." Jenny informed Nate, trusting him.

"Hey at least he's got ambition." Nate nodded thoughtfully, at least he wasn't some jerk with no ambition and a motorcycle.

"Yeah." Jenny smiled.

"So hows everything with Vanessa?" Jenny asked.

"Good, I guess." Nate furrowed his brow in confusement as he took a long drag on his joint.

"You guess?" Jenny asked, doing the same.

"Well..." Nate began.

"No, wait." Jenny said, cutting Nate off. He looked at her confused. "She's starting to become a little, possessive? Clingy? Get's mad when you hand with other people without her, always calling, texting..." At that exact moment Nate's phone went off. He looked at the screen and laughed loudly turning it so Jenny could see.

_Vanessa Calling_

Jenny laughed when she looked at the screen.

"It's like you've dated her yourself." Nate smirked.

"Dan did actually, so yeah I basically did." Jenny laughed, Nate laughed with her. About twenty minutes passed and the pair were laughing for no reason at all.

"What's so funny?" Nate laughed, clutching his stomach.

"I don't know." Jenny laughed harder, it took another ten minutes but they managed to calm themselves down. "You know, I have this theory..." Jenny began, and Nate burst out laughing. "No, no, just listen. Imagine, that Toy Story was real." Jenny began laughing hysterically.

"Follow me." Nate laughed, he tip toed so Jenny done the same. They came to a stop at the last door in the long corridor of the upstairs of Nate's huge home. Nate slowly pushed open the door and his mother had a whole bunch on China dolls on a shelf.

"They're creepy as fuck!" Jenny pulled a face of disgust. Nate got down on all fours behind the bed and Jenny did the same.

"What if they're alive? They could be watching us." Nate whispered seriously.

"Oh my god, they could want to kill us." Jenny whispered back, wide eyed, causing Nate's eyes to widen as a panic look overcame his handsome features. She peered up over to bed to the shelf and Nate done the same. They both just stared.

"That one moved!" Nate shouted jokingly, but he actually he actually freaked himself out, so he got up and ran out. Jenny screamed and began laughing nervously and ran after him. Once they were in the safety of Nate's room he locked the door.

"Should we go out and get some food? I'm starved and those dolls are fucking scary." Jenny laughed.

"Yeah." Nate nodded wide eyed, still a little freaked out. Jenny grabbed her weed and put it in her bag and zipped it up.

"Ready?" She asked.

"One second, I wanna change out my uniform." Nate said, pulling his shirt off. Jenny quickly admired his body as he began talking his trousers off.

"Been working out, Nate?" She smirked.

"Yeah, gotta keep myself buff for the ladies." Nate joked, laughing.

"Yeah yeah." Jenny laughed. "Hey you got a shirt I can wear?" She asked, she was wearing leggings, vans and a school shirt. She could change the shirt and she wouldn't have to walk around in her uniform.

"Sure." Nate turned and began rummaging through his wardrobe, so Jenny plopped herself in front of his mirror and took her pony tail down, her long blonde hair hung to the small of her back and she began applying some more eye-liner so her eyes wouldn't look so glazed.

"Here." Nate called, throwing her a white Hollister top that was far too big for her.

"Thanks." She smiled, she turned around, unbuttoned her shirt and quickly put it on. It hung to the middle of her bum and slightly hung from her left shoulder. She shoved her eye liner and school shirt in her bag when she was dressed.

"You see when I wear that shirt, I prefer to roll it up to show my belly button. I get all the guys when I wear it." Nate smirked, she looked at him before they both burst out laughing.

"You're just such a babe magnet." Jenny said sarcastically.

Nate pretended to flip his hair and strutted around his room before coming to a stop and striking a pose. "I know right, don't you forget it girl! Lock up your boyfriends ladies, Nate's on the prowl." He said in the most feminine voice he could muster, causing Jenny to laugh in hysterics.

"Get dressed." She teased, they both laughed for a bit longer before he actually made an effort to get dressed. He simply dressed in dark skinny jeans with a white Hollister top. "Twins." Jenny laughed, their shirts were similar.

"Looks better on me, sorry not sorry." Nate smirked, earning a playful slap from Jenny. He grabbed two pre rolled joints and placed one carefully in his pocket and lit one up.

"Hey you could of told me you were having another, I would of made one." Jenny pouted playfully.

"We'll share this one, next ones on you." Nate smirked, taking another drag before passing it to Jenny. It wasn't long before the pair were finished. Nate went to the kitchen and grabbed them both a can of Dr Pepper before they left. Jenny closed the door behind her. She and Nate just laughed at each other before they aimlessly walked the busy streets of New York. It was obvious they were high, they both had major red eye and they smelled of weed.

"You're so high right now." Jenny laughed as people pushed passed the pair who were walking very slowly.

"So are you." Nate looked down at her and laughed. "You ever been in there?" He pointed to a little diner.

"No." Jenny said. "It looks so cosy."

"We should go in there. It's so close and I'm so hungrrrrry." Nate laughed after dragging the word out to emphasise his hunger.

"Me too." Jenny laughed as well, they walked into the diner and took a seat and began inspecting the menu's. They both ordered a bacon, double cheeseburger each with all an extra side of fries, toppings along with two large cokes. They both waited impatiently until the the food arrived to their table, as soon as the woman placed the plates down they both stared at the food in amazement before tucking in. It was devoured within 10 minutes.

"I'm stuffed." Jenny let out a huff before pushing the empty plate aside.

"Same. Never knew you could eat like that." Nate teased, Jenny smirked.

"The munchies help me beat anorexia." She said before chuckling softly.

"Really?" Nate cocked a brow.

"Yeah. When my whole clothing line got flushed down the toilet and I pushed my friends and family away I got pretty depressed and lost a lot of weight so Dan suggested Marijuana." Jenny told him.

"Woah, Dan?" Nate said shocked. He vaguely wondered if that was why she didn't reply to his letter but decided to let it go.

"Yeah he's not the good boy everyone thinks he is." She laughed.

"I always knew there was a bad boy underneath his goody two shoes façade." Nate smiled back.

"So how many missed calls and texts you have from Vanessa now?" Jenny asked, changing the subject.

Nate laughed and pulled out his phone, his eyes widened before he laughed, sliding his phone over to Jenny, she looked and left out a whistle.

"Only 24 missed calls and 18 texts? You got it pretty easy." Jenny joked.

"She's gonna kill me." Nate shook his head, the waitress picked up both of the empty plates and looked shocked.

"Can I get you anything else?" She asked rudely.

"Just the cheque." Jenny smiled politely.

"You seriously didn't eat this all did you?" She asked Jenny with a look of disgust.

"Excuse me?" Nate said in a strong, defensive tone.

"What?" The waitress asked, clearly she was unaware she was being rude as hell.

"Lady, the cheque. Now?" Jenny snapped.

"Fucking stoners." The woman huffed before walking away.

"What a bitch!" Jenny said in shock.

"Oh, feisty one you are.." Nate said in his best Yoda impression, smirking proudly when he thought it sounded pretty good. He'd re-watched that episode of the British version of the Inbetweeners, he preferred it much better than their version. Jenny laughed and shook her head.

"What an old, miserable bitch." Jenny laughed and snorted at the same time, causing Nate to laugh with her. The woman threw the cheque down at the table before walking off. Nate put the money in the cheque book and left her with only a $1 tip. Usually, he was big on tips but the woman was just plain rude.

"A $1 tip was harsher than no tip." Jenny giggled as they left.

"Yeah." Nate chuckled. "So what do you wanna do?"

"I don't know." Jenny said, still in a stoned haze.

"Wanna go to central park?" Nate asked.

"Sure." Jenny smiled.

"Anywhere beats being at my place with those creepy dolls." Nate shuddered before they both burst out in hysterics. Both teenagers completely oblivious to the short, chubby girl taking a picture before she ran away. As they entered Central Park, they sat down on the bench and just enjoyed the quite.

"That midget is staring at us!" Nate said in what he thought was a whisper, but it was pretty loud.

"Look at it's little midget hands!" Jenny laughed in hysterics.

"Let's take a picture of the midget." Nate said, before quickly pulling his phone out and snapping a picture. He and Jenny laughed at the tiny, chubby person.

"Hey little midget!" Jenny shouted.

"Excuse me! Rude much!" A tall, thin woman appeared, grabbing the midgets hand. "She's 7 years old!" The woman snapped harshly before walking away.

"That was a child?" Nate laughed. "It looked like an Umpa Loompa." This caused Jenny to clutch her stomach and laugh. Another twenty minutes went by and they just continued to laugh about the small midget-child before they eventually calmed down and sat in a comfortable silence. That's when their phones went off at the same time, which usually meant one thing.

"Gossip Girl?" Nate said.

"Probably." They both read.

_**Game of piggy in the middle, anyone? Looks like Little J and N are making up for lost time. I wonder what N's girlfriend think of this little...soiree? The pair look a little too close for comfort, keep an eye on N, V, it's only a matter of time before Little J snatches him back. Board up your windows and grab some supplies - I can feel a storm coming, hopefully sooner than later. XOXO GOSSIP GIRL. **_

"Shit." Nate laughed, since He and Vanessa had been exclusive she was always checking up on Gossip Girl, she was bound to know about it by now.

"Yeah." Jenny laughed as well. They probably shouldn't be laughing but they were way too stoned to care.

"Vanessa's calling." Nate laughed.

"Stop laughing and answer." Jenny said giggling, trying to control herself.

"Really?" He asked.

"Yeah." She smirked.

"Okay." He took a deep breath and answered the phone. "Uh...hey Vanessa."

Jenny began giggling, Nate placed a hand over her mouth and tried not to laugh, it really took all he could to not just burst out laughing.

_"Nate! What the fuck are you doing with Jenny? She's a little bitch! I've warned you Nate!" Vanessa roared down the phone._

_"That's my little sister!" Nate heard Dan shout._

_"Shut up Dan! Fuck you, __Nate, you __better bring that little bitch home and pick me up, now!" Vanessa shouted._

Nate just laughed even harder, what had came over him?

"Hey, miss buzz-kill. Chill out, we're on our way." Nate laughed, not even bothering to hold it in any longer. He hung up the phone. "Come on Jenny, let's go to your place."

"Okay." Jenny laughed. She, Rufus and Dan moved in Lily shorty after they got back together and as much as Vanessa claimed to 'hate' pretty much everyone and everything in the UES she sure had been hanging around there a lot lately. Jenny hated it so much, Vanessa hated her guts and she was always there in Jenny's home, causing trouble between Serena and Dan. Lily and Rufus said marriage was out of the question for a long time so it wasn't too weird that they were together. Jenny often stayed at their old place though, her dad bought it out and kept it as a back up plan if anything ever went wrong but Jenny used it as an escape sometimes when she needed to do homework or just to be alone.

"Taxi!" Nate called and the taxi stopped right in front of them at the entrance of Central Park. They got in, said their destination and they set off. When they pulled in outside of Jenny's house, Dan jumped into the Taxi with them.

"Hey. To 445 Water Street, Brooklyn please. And step on it." Dan instructed quickly.

"You know this man?" The old, fat man said in a strong accent. Clearly from Brooklyn.

"Yeah." Nate and Jenny said in union.

"Okay." The man grunted before peeling away from the side walk and driving even faster than before.

"What's up?" Jenny asked.

"Vanessa's having one of her infamous hissy fits and you know what she gets like. She's been so on edge lately, she's going crazy. I locked your bedroom door and mine before making an escape down the fire exit. Wouldn't of been long before she'd realised I've left." Dan shook his head chuckling.

"She's mad, huh?" Nate said sheepishly.

"Yeah, I'd say mad's an understatement." Dan said before chuckling again, remember the furious rage he left Vanessa in. Once they were safely in the apartment they all went round closing the blinds, locking the windows and the front door, just in case she showed up.

"Door locked?" Dan asked.

"Yeah, and dead-bolted. I triple checked." Jenny said. "Windows?"

"Done, and also, triple checked." Dan said. "Blinds?"

"Done, I couldn't really triple check but they're all definitely closed." Nate laughed.

"Looks like we're spending the night here." Dan laughed, it was a Friday anyway so Jenny and Dan would of usually stayed here.

"I have video games." Dan suggested.

"I still have some movies here, don't I?" Nate asked.

"Yeah." Dan nodded pointing at him, remembering his friend left some behind when he was staying here. It didn't take them long before they became close friends again. "We're also stocked up on food, I went shopping during the week."

"Cool." Jenny smirked.

"So, I can cook." Dan smiled.

"I can pick a movie, I'm good at that. It's just this awesome talent I have." Nate said jokingly causing the siblings to laugh.

"And I have weed. Loads of it, still got my stash in my room." Jenny smirked, Nate quickly looked over at Dan and cautiously inspected his facial features. To Nate's surprise, he was smirking.

"I guess I could let loose for one night." Dan smirked.

"One night? You mean every single weekend?" Jenny teased.

"Awesome." Nate laughed.

They spent the evening lounging around, watching movies, getting high and eating. It was so nice to finally all be real friends again. Everyone put Vanessa at the back of their minds and just enjoyed themselves.


	2. Adventure Two

**Thank you to all who reviewed and followed. **

_Disclaimer: __**I own nothing.**_

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><p><strong>Adventure 2<strong>

"Morning." Dan and Nate said is unison as Jenny entered the living room, not taking their eyes away from their video game.

"Hey guys." Jenny smiled, rubbing at her eyes. "I see you guys have had a productive morning."

"Say's the one who woke up at..." Nate quickly glanced at his watch "One pm." Jenny just laughed. "Fuck!"

"Yes!" Dan exclaimed, throwing his hands in the air.

"If that creeper didn't kill me, I would of beat you... again." Nate grumbled, throwing the controller onto the couch.

"Surrre." Dan drawled out sarcastically.

"Oh, how long has this coffee been here?" Jenny asked, completely ignoring the boys as one sulked and the other boasted.

"Around ten minutes." Dan replied.

"Sweet." She replied, pouring herself a cup. "So, who's ready to face Vanessa?" She asked as she joined the boys on the couch.

"Not me." Both Dan and Nate said.

"Me neither." Jenny laughed.

"Hey Dan, you know..." Nate began, before being cut of by Dan laughing.

"Nu-uh, no chance man. We're not exactly on speaking terms either, there's no way I'm going to help patch things up with her." Dan said laughing, standing up.

"Come on, man." Nate pleaded.

"After the way she spoke about Jenny I don't think I'll be speaking too her any time soon." Dan said, sounding more serious this time. Nate just silently nodded, understanding Dan's protective tendencies toward his sister, he's seen it first hand himself. Nate looked at Jenny.

"Oh no, she hate's me enough as it is." Jenny laughed bitterly.

"True." Dan nodded with a knowing look. "But, we will have to speak to her sooner or later." Dan added.

"Later." Jenny said quickly.

"I agree." Nate laughed. "You have a point though, I should probably see her before Blair's Mom's celebration party."

"Oh crap, is that tonight?" Dan asked, his eyes almost bugging out of his head.

"Yeah, she's celebrating the success of her clothing line, remember?" Jenny said, knowing that Serena had kept on at him not to forget about this for a month now.

"I knew I was forgetting something." Dan shook his head.

"Is Serena going to be mad that you're still here?" Nate asked.

"Nah, one good thing about living with your girlfriend slash somewhat step-sister is that you can arrange everything together at home, and I don't have to pick her up seeing as she's literally just down the hall." Dan joked, a lot of people looked down on him and Serena for dating since Lily and Rufus were also in a relationship, and now living together, People saw them as step- siblings, but they weren't going to let that ruin their relationship.

"That's weird, yet brilliant." Nate laughed.

"It's like from that movie Lone Star State of Mind." Jenny smirked to herself.

"Ha ha." Dan said sarcastically giving Jenny his signature 'are you being serious' look. "Speaking of the party, is Jake still coming?" Dan asked.

"Yeah, he's picking me up and eight thirty." Jenny said, before sipping her coffee.

Nate fought the urge to ask more questions about Jake but decided it was better not too, Jenny might get the wrong idea about his curiosity.

"Cool." Dan nodded. "I guess I should get going, I need to get my suit dry cleaned asap or else Serena will castrate me." He joked light heartedly, he gathered his things and with that he was on his way.

"I'll see you tonight, man." Dan smiled to Nate. "See you at home, Jenny."

"Bye." Jenny smiled.

"Later man." Nate smiled. He looked around the couch until he finally found what he was looking for, his cell phone.

"You should call her, or at least text her." Jenny said, smiling warmly.

"She's going to kill me." Nate said, with a sigh.

"It'll be fine, I'm sure of it." She said.

Nate decided it was a good idea. He quickly read most of his messages from Vanessa, most of them were angry texts but the last few were apologetic. He quickly began texting.

_**N: Hey V. Meet me at Rufus' gallery in an hour?**_

He didn't have to wait very long for her response.

_**V: Sure thing, see u then. V xx**_

"She's going to meet me at your Dad's gallery at two thirty. She won't kill someone in public would she?" Nate joked.

"Yeah... I've seen her do it." Jenny said pursing her lips, trying to keep a straight face. Nate faked a horrified look before laughing. "I'm kidding, she'll be fine with you, she'll probably find away to put the blame on me anyway."

"I'm actually dreading it." Nate placed his large palms over his face before sighing lowly.

"Hey, I know how we can take the edge off." Jenny said, you could hear the grin in her voice. Nate chuckled into his hands before looking up.

"If you're thinking what I'm thinking, you don't have to ask me twice." Nate grinned.

"Of course I'm thinking what your thinking." Jenny laughed, she grabbed an old jewellery box and inside she had everything needed to make a joint. It wasn't long before she and Nate were on the roof, smoking and watching the flocks of people wandering the streets of Brooklyn.

"You feel better?" Jenny asked, passing Nate the joint.

"Yeah." Nate smiled lazily before inhaling a deep drag.

"Jennifer, Nathaniel." Jenny and Nate both turned to look behind them faster than they've ever moved, Nate threw the joint to the floor.

"Chuck!" Jenny shrieked her heart beating a mile a minute.

"You scared the hell out of us, man." Nate shook his head before looking around the floor.

"It's nice to see the two of you are reacquainted." Chuck nodded his signature nod, noticing the looks on their faces Chuck began speaking. "Daniel told me you were here, Blair's busy making sure Eleanor's party goes to plan and I was rather bored."

"Here." Nate said, passing the joint, he picked up from the floor to Chuck, he accepted and smirked after taking a drag. "I must buy some more of this."

"You know where to find me." Nate winked at his best friend. "Oh shit, do any of you have the time?" Nate asked, Jenny pulled out her phone.

"It's two fithteen." Jenny told him.

"Shit, I need to meet Vanessa." Nate said, mentally kicking himself. Time felt like it was going so slow, but it clearly wasn't. "I gotta go."

"Where are you meeting her?" Chuck asked.

"Rufus' gallery." Nate said.

"Perhaps I can be of assistance, Arthur's parked outside." Chuck said. "We can drive you there."

"That would be awesome, man." Nate said thankfully.

"Are you going home after?" Jenny asked, as Chuck still lived at the Van Der Woodsens.

"Yes." Chuck said, finally passing the joint back to Jenny. "If we leave now, Nathaniel can make it in time."

"Okay, I'll just grab a few things and I'm ready." Jenny said, passing what was left to Nate before hurrying inside and grabbing a few things, Nate and Chuck in tow behind her.

* * *

><p>Just as Nate had expected, Vanessa was outside waiting for him. He climbed from the limo after saying goodbye and waved them off before walking over to her. Nate began regretting the decision to smoke another joint in the limo because he was feeling very spacey, all he wanted to do was chill out and watch a funny movie, something like Step Brothers.<p>

"Hey." Vanessa smiled weakly.

"Hey." Nate smiled back, he just stared at her and she stared back giving him a strange look. _'Fuck, I'm staring. Keep it together, Archibald.'_ He thought to himself. "Shall we?" He said, gesturing to the door.

Once they ordered they sat down at a table.

"Here" A waitress said, placing a hot cup of coffee in front of him.

"Thanks." Nate smiled at the girl then turned to Vanessa "So..." He began, after being sat in awkward silence for a few minutes. Nate burst out laughing.

"What's funny?" Vanessa snapped.

"What?" Nate laughed even harder, he couldn't control himself.

"Nate this is serious. Stop!" Vanessa growled.

"Okay, okay.." He took a few deep breaths and focused his attention on a scratch on the table, running his fingers over it. Nate began to wonder how it got there, then he began to wander where tables and chairs were made, he was perfectly content getting lost into his thoughts before he saw Vanessa's hand waving in his face.

"Huh?" Nate said.

"Were you even listening?" Vanessa said, he could see the hurt in her eyes and felt bad.

"I'm sorry." Nate said. "Go on."

"Nate..." She began talking again and his mind began to trail off. Nate tried to force himself to focus on her, he watched her mouth closely as she spoke. "You do, do what I tell..." That was it, Nate lost it. He began laughing uncontrollably.

"You said - do do!" He laughed in hysterics, clutching his stomach, laughing as much as a child would of.

"Nate, stop laughing!" She slammed her hand down onto the table trying to gain control of him, he just laughed harder. "Nate are you fucking high?" Vanessa shouted, when she finally got a look at his face it was pretty obvious he was.

"You look mad." He laughed.

"I am mad, Nate! It's over, I'm done." Vanessa shouted. Even that wouldn't stop his laughing fit, which infuriated her all the more. She glared at him with such an intense glare, even in a stoned haze he knew it was time to leave. He took a few deep breaths.

"I'm sorry." Nate said quietly, after he'd managed to calm himself down. He took Vanessa's deadly silence as his que to leave.

Once Nate was out of site Vanessa released the tears she'd so desperately fought to hold back in Nate's presence. How could he laugh at her? Did he even care? Vanessa's blood began to boil with anger. This was all Jenny's fault, and Vanessa knew exactly how to get revenge. She pulled out her cell phone and dialled a number, after a few rings a low voice spoke.

"Hello?"

"Hey, it's me Vanessa." She smirked a devilish grin.

"Hey stranger, hows it going?" The boy replied.

"Fine thanks, Jake. Can I ask you something?" Vanessa raised an eyebrow mischievously.

* * *

><p>"You look beautiful, Jenny." Serena smiled as she put her earring in.<p>

"Thanks, so do you." Jenny smiled.

She wore a dress she designed herself, it was a short petite black peplum dress, she wore her long blonde hair down with loose curls, her outfit completed with some red plat-formed heels and red lipstick. Serena wore a long, white dress with gold accessories.

"Both looking beautiful ladies." Dan complimented as he walked into Serena's room where they were getting ready. "Especially you." He grinned as he pulled Serena in for a quick kiss. Serena giggled and deepened the kiss, Jenny joked a look of disgust before laughing just before she heard Jake call her from the living room, he must of let himself in.

"Saved by the bell." Jenny joked before leaving the room, Serena and Dan smiled following her.

"Hey." Jenny smiled widely, rushing over to her tall, handsome boyfriend.

"Hey yourself." He grinned before picking her up and pulling her in for a deep, welcoming kiss.

"I've missed you so much." Jenny smiled.

"Me too." Jake replied, brushing a stray strand of her hair from her face. "You look amazing."

"Thanks." Jenny said shyly. "You look great."

"Thanks." Jake laughed. "Oh, hey guys." He waved to Dan and Serena.

"Hey." The couple replied in union.

"Everyone ready?" Jake asked.

"Yeah." They all nodded, Jenny and Serena grabbed their purses and with that they were on their way out and seating themselves in the long-stretched limo that was waiting for them.

"Oh, and before I forget we're also picking up Vanessa." Jake smiled.

"What?" Jenny said, not bothering to hide the disdain in her voice.

"Huh? She asked me for a ride and... you guys are friends right? She told me you were." Jake said, clearly confused.

"Do you ever listen to me when I'm talking? I've told you we're not friends." Jenny said sadly.

"Jenny I'm sorry, I didn't know." Jake said sheepishly.

"It's okay, but I'm not riding with her." Jenny said sternly, Jake usually had a way of talking her into things, like eating at fancy restaurants or attending stupid parties for the upper class, but not this time.

"I can't just not pick her up, or let her down last minute. Look, why don't we just drive with her to the party? Once we're there we won't have to talk to her." Jake tried to compromise with her, he was far too caring of others to be rude to anyone. Serena and Dan awkwardly shifted in their seats while the younger couple spoke.

"No, look, I can ride with some other friend to the party. I'll meet you there." Jenny said, opening the door and stepping out.

"Jenny, please." Jake pleaded.

"It's fine. I'll see you there, okay?" She leaned into the car and gave her boyfriend a kiss before he directed his driver to Vanessa's place. Once they were on there way, Jenny pulled out her cell phone and dialled a number.

"Hello?" A low voice answered.

"Hey Chuck." Jenny said. "Have you left for Blair's party yet?"

"Of course, I'm already here. Is there a problem?" He asked.

"No, I just need a ride. I'll get a cab." Jenny bit her lip and nodded, of course he was already there. It's his girlfriends mother's party.

"Nathaniel hasn't arrived yet. Maybe you could call him." Chuck suggested.

"Oh, that's great. Thanks Chuck." Jenny smiled.

"No problem. See you soon." Chuck said before hanging up the phone. Jenny scrolled through her contacts before coming to a stop at Nate, she pressed dial and within a few moments he answered.

"Hey Jenny, what's up?" Nate said in a happy tone.

"Hey Nate. Have you left for the party yet?" She asked.

"Nope. Why? What's up?" He asked.

"Could I get a ride with you?" Jenny asked, trying to sound as sweet as possible.

"Sure. I'm on my way." Nate said.

"Thanks." Jenny replied before saying good bye and hanging up. She waited for ten minutes before Nate's limo pulled up in front of her. Nate's driver quickly got out of the limo before rushing to the door to open it for Jenny.

"Thank you." Jenny smiled widely at the old man.

"No problem, ma'am." The man nodded polietly before closing the door.

"Hey." Nate smiled.

"Hey." Jenny smiled back. "I can't thank you enough for this, Jake decided it would be a good idea to give Vanessa a ride, and there is no way I'm going to sit in a car with her so she can insult me." Jenny shook her head.

"How do they even know each other?" Nate asked.

"I never even thought about that." Jenny raised an eyebrow, that was a very good question. "How did it go with her today anyway?" _It probably didn't go well, due to the fact Nate was going to the party alone and Vanessa was going with Jake_, Jenny thought.

"She broke up with me." Nate said blankly. Jenny couldn't read his facial expression, he didn't look sad or happy, just blank.

"Oh, I'm sorry Nate." Jenny said sympathetically.

"It's fine, don't worry." Nate pursed his lips. "I was so baked I just laughed at everything she said, she was so mad." Nate chuckled softly.

"Oh my god, really?" Jenny laughed.

"Yeah, I don't know what came over me." Nate also laughed.

"Speaking of baked, I have a little something in my purse. You in?" Jenny smirked.

"Hell yeah." Nate laughed, his driver could clearly hear the whole conversation, the old man chuckled before rolling up the privacy window. Jenny lit the joint and took a few deep drags before passing it over to Nate.

* * *

><p>Jenny stepped out of the limo with Nate outside of one of Chuck's enormous hotels. They soon joined the party where they quickly greeted everyone before they met up with Jake, Dan and Serena.<p>

"Vanessa's at the bar." Dan quickly informed her, Jenny silently thanked her brother for making sure she wasn't with the group when she arrived.

"Nate, this is Jake. Jake, Nate." Jenny introduced the two boys.

"Hey man. Heard a lot about you." Nate smiled, shaking the slightly taller boys hand.

"Hey. You too." Jake lied, in fact, he'd never heard Jenny mention being friends with Nate Archibald, he'd read about him in the papers, apparently Jake's father knew Nate's. Jake looked over at Jenny and gave her a questioning look to which she ignored. The small group talked before they were joined by Chuck and Blair.

"I hope you're all having a good time." Blair smiled.

"This party is great, B." Serena quickly said.

"Yeah, it's amazing." Jenny smiled. Everyone else also commented on how great it was.

"Nice purse, Nathaniel." Chuck commented, gesturing toward the purse Nate was carrying.

"Thanks." He joked. "It's Jenny's, I held it for her when she got out of the limo. We both decided it looked better with my outfit than hers." Nate joked again.

"Nice to see Jenny still has that hold over you." Chuck smirked, it's just like him to try and cause trouble. Nate gave him a look as if to say 'you better shut up' while Jake gave Jenny a look to say 'what on earth does he mean by that'.

"Oh, I have to greet some new guests." Blair said before shooting off.

"I need a drink, you guys want one?" Dan said. Everyone said no so he and Serena left to go to the bar, leaving Jenny, Nate, Jake and Chuck. The conversation was somewhat laconic before two other people joined the group.

"Ah, Jacob." A very tall British man said, resting a hand on his shoulder. "Jennifer, how lovely to see you." The man smiled widely.

"Hello, Jennifer." The beautiful blonde woman smiled, she didn't look her age at all.

"Hello, Mr Smith, Mrs Smith." Jenny greeted.

"Hello father, mother." Jake smiled. "This is Nate Archibald." He didn't bother introducing them to Chuck, his parents had done business with his father so they already knew who he was.

"Ah, hello Nathaniel." The man smiled, shaking his hand.

"Hello." The woman smiled, it seemed innocent but Nate detected she was checking him out.

"It's very nice to meet you both." Nate smiled.

"We're very sorry to hear about your father." The older man nodded sympathetically.

"Thank you. Sorry I must excuse myself." Nate said, before turning to Chuck who had an entertained look on his face. "Can I speak to you?"

"Sure." Chuck smirked. "Nice to see you again." He nodded toward the older couple before following Nate to the other side of the room.

"Wow." Chuck chuckled.

"What?" Nate asked.

"Have you ever been so deep in the friend-zone, you've met her boyfriends parents?" Chuck actually laughed at this point, which was very rare for him.

"Ha-ha, you're so funny." Nate shot him a glare.

"Relax. It's not like you have any feelings for little Jennifer still, is it?" Chuck asked, raising an eyebrow.

"Of course not." Nate said surely, although over the weekend and after hanging out at the loft with Jenny again he couldn't help but think about what could of been if Jenny had responded to his letter.

"Nathaniel, I know that look." Chuck's facial expression turned more serious. Before Nate had time to think about defending himself, Blair's voice filled the room as she made a toast to her mother. The speech went on for what felt like forever, once it was finally over Jenny approached Chuck and Nate.

"Have you guys seen Jake? One minute we were talking with his parents, the next he's gone." Jenny asked, the confusion in her face pretty clear.

"No." Nate said. "We thought he was with you."

"He's probably gone to the bathroom." Chuck said.

"Yeah, you're right." Jenny nodded, not even thinking of that before.

"Have you guys seen Vanessa?" Nate asked.

"I can't say that I have." Chuck said, sipping his drink. "Excuse me, Blair." He nodded toward Blair who was signalling him over.

"I haven't seen her, but she definietly came with Jake, Dan and Serena." Jenny said.

"Should we go and look for her?" Nate asked, slightly worried as to why she would come to this party and lay low, truthfully, he was expecting her to cause a scene.

"Sure." Jenny said, they wandered around the room and there was still no sign or Vanessa or Jake.

"Should we be worried?" Nate asked, still scanning the room.

"About Vanessa, yes. About Jake, no. I trust him." Jenny said.

"Good." Nate smiled softly. "This party blows."

"Don't let Blair hear you say that." Jenny laughed.

"I won't, she'd castrate me." Nate joked.

"I agree though, it's full of old people, classical music and fancy wine." Jenny laughed.

"But... there's also weed." Nate smirked.

"You have some?" Jenny laughed. "You must be crazy bringing that stuff here."

"It's fine, we can go to the roof and no one will even know." Nate raised a suggestive eyebrow.

"Okay, but if we get caught I'm going to castrate you myself, and then tell Blair you said this party sucks." Jenny joked.

"Okay, okay." Nate laughed. "You think Serena and Dan want in on some?"

"Probably not, but they might come with us, they look as bored as we do." Jenny laughed, she and Nate went to see Serena and Dan and just like Jenny said, they both said no to getting stoned but they'd join them on the roof because the party was boring. The small group quickly made their way to the roof where they all stoped dead in their tracks when they saw Vanessa and Jake arguing.

"You want me to tell her the truth?" Vanessa threatened.

"You wouldn't." Jake said in a low, serious tone.

"Then you tell her yourself, or like I said, I will." Vanessa lowered her tone this time.

"Vanessa please." Jake pleaded.

"You still want me, don't you?" Vanessa was suddenly getting closer and closer to Jake.

"Stop." Jake said, taking a step back.

"You know, once she finds out we slept together when you were in a relationship with her, she'll dump you and you'll come running back to me anyway." Vanessa laughed bitterly.

"We should go." Dan said, placing a hand on Jenny's shoulder.

"Dan, let her have this one." Serena said, Jenny couldn't look at her friends, she felt angry and hurt and she wanted to scream.

"What's going on here?" Jenny said, calling to Jake and Vanessa.

"You want to tell her or shall I?" Vanessa asked.

"Leave, now." Jake demanded, Vanessa shook her head and walked away, only to be stopped by Serena.

"Let her go, S. I'll deal with her another time." Jenny said. "Can you leave me and Jake alone, I'll be with you shortly." Everyone agreed, going back inside.

"Jenny, please..." Jake began.

"I want to know everything, now." Jenny said, crossing her arms.

"Uh-okay." He cleared his throat. When I first met you at your Father's gallery, it was because I was into Vanessa. I knew she worked there, so I went to see her." He began.

"So, when I met you, you weren't there because you were interested in her. Is that was this relationship is based on?" Jenny said, suddenly feeling nothing but anger.

"No! That's not it. Just hear me out." He asked, when Jenny nodded her head he began explaining. "It's true, I was there to pursue Vanessa, and that's when I met you. From the moment I saw you, I was head over heels for you. After we went out a few times, Vanessa said she needed help so I went to see her, and she seduced me. You and I weren't exclusive and I've wanted to tell you but... I couldn't. That's when I found out she had a boyfriend and that's when I realised that it was you that I want." Jake said, he spoke so quickly it was hard for Jenny to keep up.

"Okay." Jenny nodded her head.

"Okay as in we're okay?" Jake asked.

"Jake, you and I both know this means we're over." Jenny said weakly.

"I thought so." He put his hands in his pockets and looked down.

" This doesn't mean we're not friends." Jenny said, trying to lighten the situation up.

"Of course we are. Come here." Jake pulled her into his warm embrace, the tightly held one another for a few minutes before he placed a soft kiss on her cheek, pulling back Jake looked into her eyes. "Can I ask you a question Jen?"

"You just did." She half smiled.

"Funny. Is there something going on between you and Nate?"

"What?! NO why would you think that?" Jenny asked shocked.

"Well you have obviously mentioned me to him but you haven't mentioned his name once to me and you two just seem to be in total sync with each other."

"Not that I owe you an explanation or anything but me and Nate weren't friends until Friday so there was nothing to mention about him, I mean we use to be really close but then not." Jenny decided to leave it at that she really didn't want to discuss what went on between her and Nate with Jake.

Jake smiled in acceptance of her answer, Jenny smiled back and then he walked away, leaving her alone on the roof top.

Once he was out of sight, her fake smile faded and tears began streaming down her face. As if on cue, Nate opened the door and once he saw her crying he ran to her and held her.

"Are you okay?" He asked, concern dripping from his voice.

"Take me home, please?" Jenny sobbed.

"You want me to punch him? Because I can do it." Nate joked, although he was half serious. Jenny giggled a little between sobs which made Nate smiled a little.

"No, I just want to go home." Jenny's voice was a hoarse whisper.

"Of course." Nate whispered back.

* * *

><p><strong>Please review and let me know what you think :) <strong>


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